Tag: M.W=0-100

1192-21-8, name is 1-Methyl-1H-pyrazol-5-amine, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. name: 1-Methyl-1H-pyrazol-5-amine

Methyl 1 -((3 -(((benzyloxy)carbonyl)amino)oxetan-3 -yl)methyl)-4-(2-chloro-5 – methylpyrimidin-4-yl)- 1 H-pyrrole-2-carboxylate (1.34 g, 2.85 mmol), 1-methyl-i Hpyrazol-5-amine (0.829 g, 8.54 mmol), CS2CO3 (2.3 18 g, 7.11 mmol) and 3rd Generation BrettPhos precatalyst (0.258 g, 0.28 mmol) in 1,4-dioxane (100 mL) was stirred under anatmosphere of nitrogen at 90 °C for 2 hours. The reaction mixture was poured into EtOAc (100 mL), washed with water (3 x 100 mL), the organic layer was dried over Na2SO4, filtered and evaporated to afford yellow oil. The crude product was purified by flash silica chromatography, elution gradient 0 to 5percent MeOH in DCM. Pure fractions were evaporated to dryness to afford methyl 1 -((3 -(((benzyloxy)carbonyl)amino)oxetan-3 -yl)methyl)-4-(5 -methyl-2-(( i-methyl-i H-pyrazol-5 -yl)amino)pyrimidin-4-yl)- 1 H-pyrrole2-carboxylate (1.07 g, 70.7 percent) as a white foam. m/z (ES+), [M+H]+ = 532.

The synthetic route of 1192-21-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; ASTRAZENECA AB; WARD, Richard, Andrew; GRAHAM, Mark, Andrew; SWALLOW, Steven; JONES, Clifford, David; (282 pag.)WO2016/162325; (2016); A1;,
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Adding a certain compound to certain chemical reactions, such as: 35277-02-2, name is 4-Fluoro-1H-pyrazole, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 35277-02-2, SDS of cas: 35277-02-2

To a solution of 4-fluoro-1H-pyrazole (0.09 g, 0.001048 mol) in anhydrous THF (5 mL), which was cooled in an ice water bath under an argon atmosphere, was added sodium hydride (60% dispersion in oil, 0.15 g, 0.003669 mol). After addition, the resulting mixture was stirred for three hours. (R)-3-Bromo-N-(4-cyano-2-iodo-5-(trifluoromethyl)phenyl)-2-hydroxy-2- methylpropanamide (0.50 g, 0.001048 mol) was added to above solution, and the resulting reaction mixture was allowed to stir overnight at room temperature under argon. The reaction was quenched by water and extracted with ethyl acetate. The organic layer was washed with brine, dried with MgSO4, filtered, and concentrated under vacuum. The product was purified by a silica gel column using hexanes and ethyl acetate (2:1 to 1:1) as eluent to afford 0.32 g (64%) of the titled compound as a white solid.1H NMR (400 MHz, CDCl3) d 9.60 (s, 1H, NH), 8.76 (s, 1H, ArH), 8.69 (s, 1H, ArH), 7.76 (d, J = 4.8 Hz, 1H, Pyrazole-H), 7.36 (d, J = 4.4 Hz, 1H, Pyrazole-H), 6.85 (s, 1H, OH), 4.39 (d, J = 14.0 Hz, 1H, CH), 4.20 (d, J = 14.0 Hz, 1H, CH), 1.41 (s, 3H, CH3).Mass (ESI, Negative): 481.00 [M-H]-;

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Reference:
Patent; GTX, INC.; UNIVERSITY OF TENNESSEE RESEARCH FOUNDATION; NARAYANAN, Ramesh; MILLER, Duane, D.; PONNUSAMY, Thamarai; HWANG, Dong-Jin; HE, Yali; (202 pag.)WO2019/222556; (2019); A1;,
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1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Formula: C4H7N3

General procedure: Amino-pyr azole 1 (0.291 g, 0.003 mol) and an aqueous solution of NaBr (100 mL) (concentrations were as follows: 1 in entries 1 and 2, 2 Min entries 3 and 5-9, and 3 in entry 4) were placed in a cell. In experiment 2, NaHCO3 (0.504 g, 0.006 mol) was added to the solution. The electrolysis was carried out at the following currents: 426 mA for entries 1-4, 213 mA for entry 5, 710 mA for entries 6, 8, and 9, and 852 mA for entry 7. In experiment 9, 48% aqueous solution of HBr was periodically added to the reaction mixture to maintain 7. After passing 2 F of electricity per 1 mole of the starting aminopyrazole 1(Q= 579 C) for entries 1-7or 8 F (Q= 2316 C) for entries 8and 9, the electrolysis was stopped, the reaction mixture was stirred for 1 h and analyzed by TLC (eluent light petroleum ether-ethyl acetate (1 : 1)). Then, the mixture obtained was diluted with concentrated HCl (to 3) and the products were extracted with CHCl3 (3×30 mL). The extracts were combined, dried with anhydrous MgSO4, and concentrated in vacuo. The products were isolated using column chromatography on SiO2 (eluent light petroleum ether-ethyl acetate). The following compounds were isolated: 1,2-bis(1-methyl-1H-pyrazol-3-yl)-diazene (7) (entries 1-7; the product was identified by m.p. 201-202 C (cf. Refs 2 and 4: m.p. 201 C) and the reported 2,41 NMR spectra) and 1,2-bis(4-bromo-1-methyl-1H-pyrazol-3-yl)diazene (8) (entries 8 and 9, the product was identified by NMR spectroscopy and high resolution mass spectrometry). The aqueous layer obtained after extraction was concentrated in vacuo, diluted with NaOH with stirring (to 10), and treated as described above. This resulted in the isolation of 3-amino-4-bromo-1-methyl-1H-pyrazole (6) (entries 1-9; the product was identifi ed by m.p. 97 C (cf. Ref. 10: m.p. 97-98 C) and the reported 51 NMR spectra) and unreacted aminopyr-azole 1(entries 1-8; the starting compound was identified by TLC and NMR spectroscopy).

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Lyalin; Sigacheva; Kokorekin; Dutova, T. Ya.; Rodionov; Petrosyan; Russian Chemical Bulletin; vol. 67; 3; (2018); p. 510 – 516; Izv. Akad. Nauk, Ser. Khim.; 3; (2018); p. 510 – 516,7;,
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Adding a certain compound to certain chemical reactions, such as: 930-36-9, name is 1-Methylpyrazole, belongs to pyrazoles-derivatives compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 930-36-9, Computed Properties of C4H6N2

Two identical reactions were carried out in parallel.To a mixture of 1 -methylpyrazole (750 g, 9.16 mol) and acetic anhydride (1.7 kg, 16.67 mol) was added concentrated H2S04 (75 g, 0.75 mol) at about 20 C. The reaction mixture was heated at about 150 C. for about 3 hrs. After cooling, the two mixtures were combined, poured into ice-water (15 L), adjusted to about pH 10 with 20% aq. NaOH and extracted with DCM (4×10 L). The combined DCM extracts were dried (Na2SO4) and concentrated to afford the title compound as a brown oil (1240 g, 72%).?H NMR (400 MHz, CDCl3) delta: 7.86 (s, 1H), 7.84 (s, 1H), 3.92 (s, 3H), 2.40 (s, 3H).GCMS mlz=109.0 [M-CH3]+

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Reference:
Patent; Pfizer Inc.; BROWN, Matthew Frank; DERMENCI, Alpay; FENSOME, Andrew; GERSTENBERGER, Brian Stephen; HAYWARD, Matthew Merrill; OWEN, Dafydd Rhys; WRIGHT, Stephen Wayne; XING, Li Huang; YANG, Xiaojing; (67 pag.)US2017/240552; (2017); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0,Some common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, molecular formula is C4H7N3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

2-Bromo-5-fluoropyridine (1) (1 .Og, 5.71 mmol), i-methyl-i H-pyrazol-3-amine (2) (554mg, 5.7immol), Xantphos (0.330g, 0.S7mmol), and 0s2003 (2.79g, 8.S6mmol) were combined in dry i,4-dioxane (i5mL). The reaction mixture was degassed with N2(g) and placed under vacuum for 10mm. Pd2(dba)3 (0.26ig, 0.28mmol) was then added and the resulting reaction mixture was heated at 9000 for 30h. It was then poured onto demineralized water (200mL), and extracted with EtOAc (3 x iOOmL). The organic phases were combined, dried over Na2SO4, filtered and subsequently concentrated in vacuo. The resulting residue was purified by flash chromatographywith EtOAc/Hexane (1:1) to provide 5-fluoro-N-(i -methyl-i H-pyrazol-3-yl)pyridin-2- amine (3) as a yellow solid (0.65g, 6ipercent).LCMS (ES): Found i93.0 [M+H].

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 1-Methyl-1H-pyrazol-3-amine, its application will become more common.

Reference:
Patent; KARUS THERAPEUTICS LTD; SHUTTLEWORTH, Stephen Joseph; TOMASSI, Cyrille Davy; CECIL, Alexander Richard Liam; MACCORMICK, Somhairle; NODES, William John; SILVA, Franck Alexandre; WO2014/181137; (2014); A1;,
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288-13-1, name is 1H-Pyrazole, belongs to pyrazoles-derivatives compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Application In Synthesis of 1H-Pyrazole

To a solution of Compound 1 (10 g, 72.5 mmol) in dry DMF (100 mL) were added pyrazole (10 g, 145 mmol), K2C03 (20 g, 145 mmol) and 18-crown-6 (2 g). The resulting solution was stirred at 130 C for 4 hours. After cooling to RT, the residue was treated with water and extracted with EA. The organic extracts were washed with water, brine, dried over anhydrous Na2SO4, filtered and concentrated to give a crude oil. The crude product was purified by recrystallization to afford Compound 2 (3.5 g, 26 %). 1HNMR (CDC13, 300 MHz) oe: 2.6-2.7 (s, 3 H), 6.4-6.5 (s, 1 H), 7.7-7.9 (m, 3 H), 8.0-8.2 (m, 3 H).

The synthetic route of 288-13-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; FORGE LIFE SCIENCE, LLC; REMISZEWSKI, Stacy; KOYUNCU, Emre; SUN, Qun; CHIANG, Lillian; (98 pag.)WO2016/77232; (2016); A2;,
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Pyrazoles – an overview | ScienceDirect Topics

Synthetic Route of 1120-82-7, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 1120-82-7 as follows.

first,4-bromobenzenamine (3.44 g,0.0200 mol) was dissolved in a CH2Cl2 solvent (30.0 mL). 1H-1-pyrazolyl-1-methanol (3.92 g, 0.0400 mol) was dissolved in a CH2Cl2 solvent (20.0 mL) and added. The reaction was carried out at room temperature for 24 hours, the water was removed by solution reaction with MgSO4,The solution was removed by pressure. A green solid was obtained after distillation under reduced pressure. (5.89 g, 88.7%).

According to the analysis of related databases, 1120-82-7, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Kyungpook National University Industry-Academic Cooperation Foundation.; Lee, Hyo Sun; Jung, Jong Hwa; Choe, Sung Hey; Cho, Jae Won; (24 pag.)KR2017/51867; (2017); A;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 14521-81-4, The chemical industry reduces the impact on the environment during synthesis 14521-81-4, name is 3-Fluoro-1H-pyrazole, I believe this compound will play a more active role in future production and life.

A mixture of (5)-S -chloro-N-( 1 -cyclopropyl-2,2,2-trifluoroethyl)-7-methylpyrazolo[ 1,5 -aj pyrimidine-3 -carboxamide (70 mg, 0.21 mmol), 3-fluoro- 1H-pyrazole(18 mg, 0.21 mmol), and K2C03 (58 mg, 0.42 mmol) in DMF (2 mL) was stirred at 60 C for 2 h, poured into H20 (10 mL), and extracted with EA (30 mL x 3). The combined organic phases were washed with H20 (50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel columnchromatography (PE/EA = 2/1) and preparative HPLC (10 mM NH4HCO3/MeCN) to afford thetitle compound (14 mg, 24%) as a white solid. ?H NMR (400 MHz, MeOD-d4): 5 8.59 (s, 1H),8.55 (t, J= 2.4 Hz, 1H), 7.65 (s, 1H), 7.44 (q, J= 2.8 Hz, 1H), 4.36-4.30 (m, 1H), 2.92 (s, 3H),1.40-1.34 (m, 1H), 0. 82-0.75 (m, 1H), 0.70-0.58 (m, 2H), 0.52-0.46 (m, 1H). LC-MS m/z:383.1 [M+Hj. HPLC: Purity (214 nm): 93%; tR= 8.83 min.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 3-Fluoro-1H-pyrazole, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GOOD, Andrew, C.; (391 pag.)WO2017/176960; (2017); A1;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Reference of 1904-31-0, These common heterocyclic compound, 1904-31-0, name is 1-Methyl-1H-pyrazol-3-amine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred suspension of 1-methyl-1H-pyrazol-3-amine 76a (0.5 g, 5.1 mmol) in toluene (20 mL) in an round bottom flask fitted with Dean-Stark apparatus was charged with hexane-2,5-dione (0.70 g, 6.1 mmol) followed by p-toluene sulfonic acid (0.097 g, 0.51 mmol) and the reaction mixture was heated at 115°C for about 6 h. The reaction mixture was cooled to room temperature. Reaction mass was concentrated fully under reduced pressure, residue obtained was dissolved in DCM, given water wash followed by brine wash, dried over Na2504 and concentrated under redcued pressure to obtain 3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole 76b (0.55 g, 55percent yield) as green oil. 1HNMR (400 MHz, CDC13): 6 7.39 (d, 111), 6.15 (s, 1H), 5.85 (s, 2H), 3.92 (s, 3H), 2.10 (s, 6H), MS: 176.11 (M+H).

The synthetic route of 1904-31-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; JUBILANT BIOSYS LIMITED; VENKATESHAPPA, Chandregowda; SIVANANDHAN, Dhanalakshmi; BAKTHAVATCHALAM, Rajagopal; KETHIRI, Raghava Reddy; VISWANADHAN, Vellarkad Narayana; GIRI, Sanjeev; WO2015/25197; (2015); A1;,
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Pyrazoles – an overview | ScienceDirect Topics

Reference of 31108-57-3, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 31108-57-3, name is 1H-Pyrazole-4-carbonitrile belongs to pyrazoles-derivatives compound, it is a common compound, a new synthetic route is introduced below.

Example 118: N-(5-(4-Cyano-lH-pyrazol-l-yl)pyridin-3-yl)-2-((5-(trifluoromethyl)pyridin-2- yl)amino)isonicotinamide. To an oven dried vial with a stir bar, N-(5- bromopyridin-3 -yl)-2-((5 -(trifluoromethyl)pyridin-2-yl)amino)isonicotinamide (0.02 g, 0.046 mmol), RockPhos (0.428 mg, 0.913 (0.042 g, 0.046 mmol),lH-pyrazole-4-carbonitrile (4.25 mg, 0.046 mmol) and K3P04 (9.69 mg, 0.046 mmol) were added. The solid mixture was purged with N2 (degassed and flushed) (3x). Then tBuOH (lmL) was added. The vial was degassed and flushed with N2 (3x) and the vessel was capped and placed in a preheated oil bath at 120 C for 5 hrs. The reaction mixture was diluted with ethyl acetate and washed with ammonium chloride. The org layer was dried over sodium sulfate, filtered and then concentrated. The residue was purified by prep LCMS to give desired prod. 1H NMR (500 MHz, DMSO-d6) delta ppm 11.02 (br. s., 1 H) 10.55 (s, 1 H) 9.48 (s, 1 H) 8.98 (d, J=1.83 Hz, 1 H) 8.90 (d, J=2.14 Hz, 1 H) 8.84 (t, J=2.29 Hz, 1 H) 8.65 (s, 1 H) 8.52 (d, J=5.19 Hz, 1 H) 8.48 (s, 1 H) 8.28 (s, 1 H) 8.07 (dd, J=8.85, 2.44 Hz, 1 H) 7.90 – 7.98 (m, 1 H) 7.51 (dd, J=5.19, 1.22 Hz, 1 H). MS (ESI) (m/z): 451.1(M+H)+.

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, 1H-Pyrazole-4-carbonitrile, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; LUO, Guanglin; CHEN, Ling; DUBOWCHIK, Gene M.; JACUTIN-PORTE, Swanee E.; VRUDHULA, Vivekananda M.; PAN, Senliang; SIVAPRAKASAM, Prasanna; MACOR, John E.; WO2015/69594; (2015); A1;,
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Pyrazoles – an overview | ScienceDirect Topics